


Letter to the Director of Admissions

by Aria_Lerendeair, StarlightDragon



Series: The Director of Admissions [1]
Category: Supernatural
Genre: Alternate Universe - Human, Bisexual Dean, Fluff and Angst, Gay Castiel, Happy Ending, Letters, Love Confessions, M/M, Past Relationship(s), Reunions
Language: English
Status: Completed
Published: 2016-03-15
Updated: 2016-03-15
Packaged: 2018-05-26 20:42:01
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,916
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6255100
Author URL: https://archiveofourown.org/users/Aria_Lerendeair/pseuds/Aria_Lerendeair, https://archiveofourown.org/users/StarlightDragon/pseuds/StarlightDragon
Summary: <blockquote class="userstuff">
              <p>When Dean Winchester's daughter is rejected from her first choice college, he decides to write to the Director of Admissions, begging them to reconsider. He doesn't expect to actually be writing to his high school sweetheart who he hasn't spoken to since graduation. These are fifty letters shared between the two of them over the following months.</p>
            </blockquote>





	Letter to the Director of Admissions

**Author's Note:**

> If you're my creative writing professor: Congratulations, you've discovered my secret. I did indeed hand this into you as one of my assignments with the names changed, and I also went the whole term conveniently without mentioning that I'm actually a fanfiction writer, and for that I apologize, and I very much hope this doesn't affect my grade or your opinion of me.
> 
> If you're not my creative writing professor: hey, here's a fic I wrote, enjoy!!

**-1-**

Dear Sir or Madam,

I am writing on behalf of my daughter, who was rejected from your university this year. Ever since she was a young child, she has been dreaming of attending Cornell, dreams which her mother and I have always supported her in. She has worked exceptionally hard all through high school, taking many AP classes, maintaining an excellent GPA and participating in a wide range of extracurriculars, despite the disadvantage that attending a public school gives her, and I and her mother feel that your rejection of her from your university was both premature and unfair, and would urge you to reconsider. She would be an excellent student and a credit to your institution.

Best wishes,

Dean Winchester (father of Katie Winchester)

 

**-2-**

Dear Mr Winchester,

Thankyou for getting in touch with the Cornell University Admissions Office. Unfortunately we are unable to honor your request to grant your child admission to the university. As you can imagine, we receive several hundred letters such as yours from rejected applicants and their families, and if we were to admit applicants based on these letters, it would set a dangerous precedent. If your child still wishes to attend Cornell, they are encouraged to re-apply next year as a transfer student.

Best wishes,

Castiel Novak (Director of Admissions.)

 

**-3-**

Dear Mr Novak,

I know you. You and I went to high school together. At least I'm assuming it's you; I don't think Castiel Novak is a very common name, and considering you went to Cornell after we graduated, it fits. I have so many memories of the two of us together, back in the day. I really hope you're doing well these days, and seriously, it'd be awesome if you could take another look at Katie's application. 

Best wishes,

Dean Winchester.

 

**-4-**

Dear Mr Winchester,

Congratulations, you made it to the second round! This means you get a personal letter written by me and not the stock photocopy we send out to everyone! This one hasn't been read over by any of my superiors so expect plenty of snark as I inform you that trying to fabricate a connection between us in high school does not increase your daughter's chances of being accepted to the university. In fact, it's not even the most creative reason I've heard this year! One woman claimed to have contacts with the Prince of Norway and insisted she could have me married into the royal family if I offered her son a place at Cornell. I did consider the offer. Admissions season is more than enough to make me desperate to move to the other side of the world.

Your daughter will not be attending Cornell.

Castiel Novak.

 

**-5-**

Dear Mr Novak,

There's no way that's a true story about Norway. I mean, I've heard of people offering to build schools a new library or something, but a place in the royal family? You made that one up.

And you want to know how I know that? Because, like I said, we went to high school together. You used to make up some pretty hilarious stories there too. Made me laugh every day, you did. Good times.

You're wasted as an admissions counselor. You'd be way better at interacting with students personally. Maybe as a creative writing teacher.

Best wishes,

Dean Winchester.

 

**-6-**

Mr Winchester,

Please kindly refrain from contacting me again.

Castiel Novak.

 

**-7-**

Cas-

Okay, okay, I know you said not to contact you again, but I figured you still thought I was lying. So here's a copy of a page from our high school senior yearbook.  That's you and me at prom together. It was the eighties and I can't believe I ever wore my hair like that but the picture of you holds up pretty well - looks like you weren't sucked into all the Eighties fashion trends, huh? Anyway, if you still don't remember me after reading this letter and seeing the pictures, then I'll drop it. But, I guess I wanted you to know that I really wasn't trying to take advantage of you.

Katie has accepted an offer from Boston College, and she is very excited.

Dean.

 

**-8-**

Dear Dean.

When I told you not to contact me in your last letter, it wasn't because I didn't remember you. Of course I remembered who you were. And there was absolutely no need for you to send me that yearbook picture. I still have the Class of 1988 yearbook, and as soon as I started getting your letters I found it and searched through it for every single picture of you. Then I scribbled on them all with red pen and the word 'Asshole'.

I repeat. Please do not contact me again.

Castiel.

 

**-9-**

Cas-

I'm really sorry, okay? I know things didn't end great for us in high school, but that was nearly thirty years ago now. And it was my ex-wife who made me send that first letter to you, even though I told her it wouldn't accomplish anything, and then when it turned out to be you who I was writing to, it felt like a sign that maybe we were meant to get back in contact with each other. You and I were something pretty special once, after all - weren't we?

Dean.

 

**-10-**

Dear Dean.

Wow.

That's pretty much all I have to say after reading your last letter. You seem to forget that, as we have already established, I know you. A 'sign'? Things that were 'meant to happen'? I saw you use those lines on so many kids that we went to school with. Hell, I fell for those lines myself once. I absolutely will not let it happen again. I am glad to hear that you're well, I truly am, but I'm not sure that getting back in contact is a good idea for either of us.

Castiel.

 

**-11-**

Cas-

I want to apologize. I'm not very good with words beyond all those lines that you already know. I do know that in high school your favorite musical was Little Shop of Horrors and I also know that it's playing not far from where you live, so I'm enclosing two tickets to the Friday evening showing next week. Take someone cool. Or sell them and keep the money, I don't care. I just wanted to do something as a very, very late apology.

All the best.

Dean.

 

**-12-**

Dear Dean.

I hadn't thought about that show for years until you sent me the tickets. Actually, I almost didn't go, because I didn't think it would be any good in comparison to how I remembered it, but at the last minute I decided to take a chance. I asked my colleague Ash to go with me. It was supposed to be a date, but we ended up just spending time together as friends, and we worked better that way. We both had an excellent night, loved the show and went for drinks afterwards. It was nice to get a break from work considering how busy things always are at this time of year.

I don't know why I'm telling you all this.

All the same, thankyou for the tickets. You didn't have to.

Cas.

 

**-13-**

Cas-

No problem at all. I'm really glad you enjoyed your night. 

Actually, can I make a confession?

This isn't a conversation so I'm going to assume you said 'yes' between the last line and this one and I'm just going to tell you. I always wanted to take you to see that show. I used to look up tickets and see how much they cost and tried to figure out the logistics of how to get us to an actual city and back in time for curfew.

I probably could have figured it out if I'd asked my parents for help, but I was always too scared of what they'd think of me if I told them I wanted to take a boy to a musical.

Thirty years on, I finally made it happen. Kind of. Guess I should be proud of myself.

Dean.

 

**-14-**

Dear Dean,

I never knew that. Never would have guessed it either. I always thought your idea of romance was spraying air freshener in that alcove behind the lockers before you dragged me off to make out there. Which wasn't something that I ever complained about, of course, but... learning something like this certainly changes my perspective on our high school experience. 

Thankyou. It means a lot to me that you tried back then.

Cas.

 

**-15-**

Cas-

I chose that air freshener especially for you! Summer Berry Blast isn't something I'd let just anyone smell while we made out.

(Yes, I still make jokes when things start to get too serious. It's a flaw. I know.)

Dean.

 

**-16-**

Dear Dean,

Does Katie still want to go to Cornell? It's not exactly orthodox, but I can try to find a place for her on the waitlist. It wouldn't be a guarantee, but... I want to do something in return for you getting those tickets for me. And I know how important her future is to you.

Cas.

 

**-17-**

Cas-

She does not. Katie is very happily settled on Boston and has already made some new friends online who are going to be there with her in the fall. She doesn't want the uncertainty right now of not knowing where she'll end up - she likes to be able to plan things. She thanks you for the offer, but she's fine with her current decision.

Dean.

 

**-18-**

Dear Dean,

Did you actually ask her, or are you just putting words in her mouth?

I know how to tell when parents are bullshitting. This is college. It's the biggest decision she'll ever make and it should be her decision.

Cas.

 

**-19-**

Cas-

I know it's her decision, but I didn't want you to think I was playing the long game, and still just using the connection we used to have to try and get Katie a place. I didn't want to be the story you told next year in place of the Prince of Norway, you know?

I'll talk to her.

Dean.

 

**-20-**

Dear Dean,

Don't flatter yourself. You could never be as interesting as the Prince of Norway. That will always be my most interesting story.

Cas.

 

**-21-**

Cas-

Well, I spoke to Katie, and this time I can confirm for definite that she is happy with Boston. She told me to, and I quote, "say thankyou to your weird old ex-boyfriend." Just passing on the message.

Dean.

 

**-22-**

Dear  Dean,

You can tell your daughter that I am only two months older than you, although, I am certainly not going to deny the accusation of 'weird'.

Cas.

 

**-23-**

Cas-

I refuse to be the go-between for you and my daughter. If you want to talk to her, find her on Tweeter or whatever the kids are using on the internet these days.

That said, if it's me you want to talk to, feel free to keep writing.

Dean.

 

**-24-**

Dear Dean,

I believe the name of the website is Twitter, and I did indeed search for your daughter's profile! Oh, you wouldn't believe the things I found out...

I'm joking, of course. She seems like a lovely girl. That was just my little bit of revenge, which I think we can both agree I earned.

How is life treating you these days, aside from being a parent?

Cas.

 

**-25-**

Cas-

You are a cruel man, and you don't even have kids, so you don't even know quite how cruel you are.

Life is good. Never dull in the city, of course. But people will always need their cars repaired, so plenty of business. How about you?

Dean.

 

**-26-**

Dear Dean,

Believe me, I know just how dangerous I am. I deal with parents every day. Some, amazingly, are even more protective than you.

It surprises me that you ended up in the city. When we were young I always saw you as the long winding roads, converted barn, country kind of guy.

Cas.

 

**-27-**

Cas-

You use your powers for evil. I admire that. But I still say you could be way more than just the school's gatekeeper. You ever considered doing anything else?

I always thought I was a country guy too, but when I got married, my wife said she'd get bored anywhere but the city. After we split, I didn't want Katie to have to move school districts, so I stayed. Maybe I'll move one day, who knows.

Dean.

 

**-28-**

Dear Dean,

I have actually applied for teaching positions, but sadly the average GPA for students finishing their first year has increased by 0.12 since I was hired, so they refuse to let me leave my current position.

If you don't mind my asking - and because I'm far nosier in a letter than I would dare to be in person - why did you and your wife separate?

Cas.

 

**-29-**

Cas-

You hold all the power in this situation. You could threaten them and say that you'll let in bad people if they don't give you the job you want. Threaten to drop the freshman GPA by a whole 0.13!

We grew apart. I know how cliche that sounds, but I guess we just got to this point where we lived together, but we only talked because we had to, about bedtimes and electricity bills and stuff, not because we wanted to. So we just let each other move on. Simple as that. (She's remarried now.)

Dean.

 

**-30-**

Dear Dean,

I'm not a legal expert, but I did hear once of something called 'blackmail' which sounds remarkably similar to the course of action you are suggesting here.

I understand. I'm glad the situation wasn't too horrible for either of you. To continue with my apparent trend of inappropriately invasive questions - she may be remarried now, but how about you?

Cas.

 

**-31-**

Cas-

Don't worry about it. My brother's a lawyer, I'm sure he'd be able to get you off the hook. Might even be able to get you the family discount if I play my cards right.

I'm single, and there hasn't been anything serious since the split. I did go out on a few casual dates, but Katie still needed a babysitter back then, work was busy, it wasn't the right time. More vague plans for the future, I guess.

Dean.

 

**-32-**

Dear Dean,

I will certainly consider it. It's always good to know people who would support and help me form my own criminal network. (I really hope the FBI are not reading my mail.)

You should start dating again. I know I'm hardly one to talk, but back in high school you certainly had no problems, and you can't have lost all your looks. Seize the day; I'm sure you'll have no problem getting a date.

Cas.

 

**-33-**

Cas-

Of course, I'm always happy to help out a friend with their criminal empire. Unless the FBI are reading this, in which case, I fully plan to turn you over to the police immediately.

There is someone I've been considering asking out, actually. I don't know if they'd be interested. It's kind of a complicated situation, but I think it might be worth the risk - should I go for it?

Dean.

 

**-34-**

Dear Dean,

Why are we sending letters to each other like this?

I mean it. This is crazy. Pardon my language, but what the fuck are we doing? We're using an outdated form of communication to do nothing but bring up bad memories of the past. I don't think this is healthy for either of us.

High school was a different time. I'm not saying I don't wish things had gone differently then, but I've had plenty of time to come to terms with it all, and I think we should both move on.

Ash and I are going out again this weekend. We are going to try again to make it into a date.

I wish you and your daughter all the best in your futures.

Cas.

 

**-35-**

Cas-

If that's what you think is best, then I'll stop sending these letters. I really did enjoy talking to you again, even if you were rude to me half the time. I guess you being rude to me is still preferable than you not talking to me at all, huh? 

Hope your date with Ash goes well.

Dean.

 

**-36-**

Dear Dean,

You don't learn from your mistakes, do you?

Cas.

 

**-37-**

Cas-

What the hell are you talking about?

Dean,

 

**-38-**

Dear Dean,

Let me tell you a story.

Back in high school, I dated this guy. He was kind of out of my league, I always thought, but he seemed to like me. Maybe because I was scared of him, I put up with more of his crap than I should have done, but mostly things were good between us.

In case you didn't figure it out yet, this guy is you.

When we finished high school, after graduation, I went to see you. I was going off to college a thousand miles away and you were staying in the same town we grew up in, so I said that even though we'd had an amazing time together, it was probably best if we broke up. You agreed.

You didn't even look upset. You definitely didn't try to fight for me. Even though I'd been the one to suggest it, it really hurt, because it felt like over a year spent together was just something you could wave away with the same goodbye you gave me at the end of school each day.

The next night I went to a party and it wasn't even ten PM when I walked in on you having a threesome with Lisa and Cassie from the cheerleading team.

I was terrified of moving away from home. I had five older brothers who had all stayed living with my parents after they graduated, gone to work for my dad, been the perfect sons, and then there was me, studying English Literature halfway across the country. Could I possibly have been a bigger disappointment? I showed up at Cornell and I was so scared and alone and nobody even spoke to me on the first day of orientation and I got back to my dorm to find my new roommate already passed out drunk with vomit in the trashcan and I cried. I wondered to myself if there was anyone I could call and you were the first person that I thought of, but I didn't think you actually cared.

I knew all along that you and I were never going to end up together. I knew it was a high school relationship that wouldn't last. But it still meant something to me, and as pathetic as it sounds, it would have been nice to know that I was more than the guy you experimented with when you were seventeen.

Cas.

 

**-39-**

Cas-

You are.

Dean.

 

**-40-**

Dear Dean,

There were two words in your last letter and they didn't impress me as much as you probably expected them to.

Cas.

 

**-41-**

Cas-

I told you I'm not good with words. How about another present? Here's a Barnes and Noble gift card, just in case you still do that thing you used to do, where you want to read a hundred different books but refuse to actually buy them for yourself.

Dean.

 

**-42-**

Dear Dean,

'Not good with words' isn't an excuse any more. You can't buy me back. I'm not a desperate college freshman now. I have a job and a boyfriend and I'm doing well. If you actually do care about me then it's going to take more than just that.

Cas.

 

**-43-**

Cas-

All the pictures of you in the yearbook are black and white, but my mind colors them in. I still remember everything about the way you looked. Your eyes looked like a painting I saw once of the waves on the sea crashing into the sky, every different shade of blue colliding together at once. You're laughing in one of the pictures - I like to pretend it's at something I said - and I hear the laugh playing over and over in my head. If I imagine you laughing right before I put the light out at night, I go to sleep with a smile on my face, and things are just a little easier because of it. It sounds like wind chimes in the breeze.

I miss you so fucking much. You want to know the reason I didn't let myself get upset when you left? Because I thought that you'd go off to college and find someone ten times better and smarter than me and you'd want to be with him instead. I thought if I got sad, you might stay with me out of guilt, and that was the worst thing I could imagine. I didn't want to be the dumb boyfriend back home who was always dragging you down and stopping you from living your life. I wanted you to be happy, whether or not that involved me. 

But, hell, sometimes I think about what things would have been like if we had stayed together. And if you'd been the one I'd married, I don't think we would have grown apart. I think we'd sit together every day on a bale of hay in our converted barn and feed each other strawberries and listen to the soundtracks of musicals and then we'd go for a drive along the narrow country roads and sit on the roof of your old car for hours and watch the stars. I think we'd have made it.

Holy shit, that was sentimental. I can't possibly send this. I should burn it before anyone else sees that I have these kind of thoughts.

Dean.

 

**-44-**

Dear Dean,

I'm glad you didn't burn it.

Cas.

 

**-45-**

Cas-

Now who's not good with words?

Dean.

 

**-46-**

Dear Dean,

Alright, alright, I suppose I deserved that. I mean it, though. I had absolutely no idea that you still thought of me like that, or that you ever did. It'd be enough to go to most guys' heads and make them feel special. 

For what it's worth? I think we'd have made it too. I see a million kids come into Cornell swearing they're going to stay with their high school sweethearts forever, and almost all of them break up by the time they've finished freshman year. It's enough to make anyone cynical about relationships. But I think we'd have beaten the odds.

When it comes to us, I'll always be a hopeless romantic.

Cas.

 

**-47-**

Cas-

Where do we go from here?

Dean.

 

**-48-**

Dear Dean,

Dinner sounds like an appropriate next course of action. I've heard the River Peasant, near you, does excellent fish. How about the Friday after next, eight o'clock?

Cas.

 

**-49-**

Cas-

I'm a middle aged man, divorced, with a kid. I'm far too old and boring for cute first dates in quirky bistros by the lake.

Yes.

Dean.

 

**-50-**

Dear Dean,

I'm technically too old for those things too - but if we think of it as picking up where we left off, then we'll both be just right.

See you Friday.

Love, Cas.

 

**Author's Note:**

> It's finals week, so cheer me up by following **casandsip.tumblr.com!**

**Works inspired by this one:**

  * [A Date with the Director of Admissions](https://archiveofourown.org/works/6259012) by [Aria_Lerendeair](https://archiveofourown.org/users/Aria_Lerendeair/pseuds/Aria_Lerendeair), [StarlightDragon](https://archiveofourown.org/users/StarlightDragon/pseuds/StarlightDragon)




End file.
